This invention relates generally to insecticidal compounds and methods for their use in controlling insects. In particular, it pertains to insecticidal oximino and hydrazono derivatives of N-benzyl-4-benzhydryl- and N-benzyl-4-benzhydrolpiperidines where the oximino and hydrazono groups are substituted at the 4-position of the benzyl ring, and the corresponding N-oxides of the piperidines. This invention also pertains to the agriculturally acceptable salts of these compounds and their compositions that are useful in controlling insects in agricultural crops.
There is a continuing demand for new insecticides that are safer, more effective, and less costly. Insecticides are useful for controlling insects which may otherwise cause significant damage to crops such as wheat, corn, soybeans, potatoes, and cotton, to name a few. For crop protection, insecticides are desired that can control the insects without damaging the crops, and that have no deleterious effects to other living organisms, such as mammals.
U.S. Pat. Nos. 5,569,664 and 5,639,763 disclose a class of piperidine derivatives for use as insecticides: ##STR1## in which, among others, U is --(CH.sub.2).sub.n -- where n is 1, 2, or 3;
Q is fluoro or hydroxy; PA1 R is selected from a heterocycle having 5 or 6 ring atoms, optionally fused to a benzene ring, and ##STR2## where V, W, Y, and Z are hydrogen; and, PA1 X is hydrogen, hydroxy, halogen, alkyl, alkoxyalkyl, alkoxy, cycloalkylalkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, alkylsilyloxy, alkylthio, haloalkylthio, cyano, cyanoalkoxy, nitro, amino, monoalkylamino, dialkylamino, alkylaminoalkoxy, alkylcarbonylamino, alkylcarbonyl, alkoxycarbonylamino, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyloxy, phenyl, phenylalkoxy, phenoxy, phenoxyalkyl, or a five- or six-membered heterocycle; each cycloalkyl moiety, heterocycle, or phenyl ring is optionally substituted with halogen, alkoxy, or haloalkoxy; PA1 W and X taken together may be --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OC(CH.sub.3).sub.2 O--, --N.dbd.C(C.sub.2 H.sub.5)O--, or --CH.dbd.CHCH.dbd.C--; PA1 R.sup.1 and R.sup.2 are independently selected from phenyl substituted with one or more haloalkyl or haloalkoxy. PA1 R.sup.1 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl and alkylaminocarbonyl; PA1 Q is fluoro or hydroxy; PA1 X is oxygen or NR.sup.2 ; PA1 Z is halogen, haloalkyl, haloalkoxy, pentahalothio, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, and --OCF.sub.2 O-- attached to two adjacent carbon atoms of the phenyl ring; PA1 n is 0 or 1; and, PA1 when X is NR.sup.2, R.sup.2 is hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl, or R.sup.1 and R.sup.2 taken together is --C.sub.m H.sub.2.spsb.m, or --C.sub.2 H.sub.4 OC.sub.2 H.sub.4 --, where m is 3-9.
The '664 and '763 patents do not disclose insecticidal oximino or hydrazono derivatives.